JPH0759536B2 - Method for producing 2-phenylisopropylamine - Google Patents
Method for producing 2-phenylisopropylamineInfo
- Publication number
- JPH0759536B2 JPH0759536B2 JP3518387A JP3518387A JPH0759536B2 JP H0759536 B2 JPH0759536 B2 JP H0759536B2 JP 3518387 A JP3518387 A JP 3518387A JP 3518387 A JP3518387 A JP 3518387A JP H0759536 B2 JPH0759536 B2 JP H0759536B2
- Authority
- JP
- Japan
- Prior art keywords
- phenylisopropylamine
- phenylisopropyl
- parts
- ammonia
- selectivity
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 38
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 22
- 229910021529 ammonia Inorganic materials 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 8
- FRCFWPVMFJMNDP-UHFFFAOYSA-N n-propan-2-ylaniline Chemical compound CC(C)NC1=CC=CC=C1 FRCFWPVMFJMNDP-UHFFFAOYSA-N 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000010410 layer Substances 0.000 description 14
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 11
- 238000003756 stirring Methods 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 7
- 230000032683 aging Effects 0.000 description 7
- 238000004817 gas chromatography Methods 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- 229910001220 stainless steel Inorganic materials 0.000 description 7
- 239000010935 stainless steel Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- -1 For example Chemical class 0.000 description 1
- QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical compound C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】 ＜産業上の利用分野＞ 本発明は、医薬、農薬、その他有機合成原料として重要
な２−フェニルイソプロピルアミンの製造方法の改良方
法に関する。DETAILED DESCRIPTION OF THE INVENTION <Industrial field of application> The present invention relates to an improved method for producing 2-phenylisopropylamine, which is important as a raw material for medicines, agricultural chemicals and other organic synthesis.
＜従来技術＞ 従来、２−フェニルイソプロピルアミンの製造方法とし
ては、２−フェニルイソプロピルクロライドをアンモニ
アによりアミノ化する方法が知られている（例えば、ケ
ミカルアブストラクト、第12巻、P.1467、特開昭48−36
129公報など）。<Prior Art> Heretofore, as a method for producing 2-phenylisopropylamine, a method of aminating 2-phenylisopropyl chloride with ammonia has been known (for example, Chemical Abstracts, Volume 12, P. 1467, JP-A No. 1994-242242). 48-36
129 etc.).
＜発明が解決しようとする問題点＞ しかしながら、２−フェニルイソプロピルクロライドを
アンモニアによりアミノ化する方法では、α−メチルス
チレンの副生が多く、２−フェニルイソプロピルアミン
への選択率は、高々60％程度である。更に回収α−メチ
ルスチレンを２−フェニルイソプロピルクロライドへの
原料として再使用する場合には、不純物が多く、精製を
必要とする等、工業的に有利な方法とは言えない。<Problems to be Solved by the Invention> However, in the method of aminating 2-phenylisopropyl chloride with ammonia, there are many α-methylstyrene by-products, and the selectivity to 2-phenylisopropylamine is at most 60%. It is a degree. Furthermore, when the recovered α-methylstyrene is reused as a raw material for 2-phenylisopropyl chloride, it is not an industrially advantageous method because it contains many impurities and requires purification.
＜問題点を解決する手段＞ 本発明者等は、２−フェニルイソプロピルアミンを工業
的に有利に製造する方法を開発すべく種々検討した結
果、２−フェニルイソプロピルブロマイドを出発原料と
して用い、特定の条件下で、アンモニアと反応させるこ
とにより、驚くべきことに高反応率、高選択率で２−フ
ェニルイソプロピルアミンを工業的に有利に製造できる
ことを見い出し、本発明を完成した。<Means for Solving Problems> As a result of various studies to develop a method for industrially producing 2-phenylisopropylamine, the present inventors have used 2-phenylisopropyl bromide as a starting material, and The present invention has been completed by surprisingly finding that 2-phenylisopropylamine can be industrially advantageously produced with a high reaction rate and a high selectivity by reacting with ammonia under the conditions.
即ち、本発明は、２−フェニルイソプロピルブロマイド
を、不活性有機溶媒の存在、又は不存在下、アンモニア
と反応させることを特徴とする２−フェニルイソプロピ
ルアミンの製造方法である。That is, the present invention is a method for producing 2-phenylisopropylamine, which comprises reacting 2-phenylisopropyl bromide with ammonia in the presence or absence of an inert organic solvent.
ここで、アンモニアの使用量は、２−フェニルイソプロ
ピルブロマイド１モルに対し、２モルより少ないと２−
フェニルイソプロピルアミン選択率の低下、α−メチル
スチレンの副生が増加する傾向を示し、一方、２−フェ
ニルイソプロピルブロマイド１モルに対し、アンモニア
を10モルより多く用いることは、容積効率が悪くなり、
経済的な面で得策とは言えない。Here, when the amount of ammonia used is less than 2 mol per mol of 2-phenylisopropyl bromide, 2-
The phenylisopropylamine selectivity tends to decrease and α-methylstyrene by-product tends to increase. On the other hand, when more than 10 mol of ammonia is used per 1 mol of 2-phenylisopropyl bromide, the volume efficiency becomes poor,
It is not a good idea financially.
従って、アンモニアの使用量は、２−フェニルイソプロ
ピルブロマイド１モルに対し、２〜10モル、好ましく
は、３〜８モルが適当である。Therefore, the amount of ammonia used is 2 to 10 mol, preferably 3 to 8 mol, per 1 mol of 2-phenylisopropyl bromide.
反応温度は、高過ぎるとα−メチルスチレンが多く副生
し、目的物である２−フェニルイソプロピルアミンへの
選択率が低下する。一方、反応温度が低いと、選択率は
高くなるものの、反応系の粘度が上昇し、攪拌混合が不
十分となる。If the reaction temperature is too high, a large amount of α-methylstyrene is by-produced, and the selectivity for 2-phenylisopropylamine, which is the target, decreases. On the other hand, when the reaction temperature is low, the selectivity increases, but the viscosity of the reaction system increases and stirring and mixing become insufficient.
従って、反応温度は通常−10〜50℃、内でも−５〜20℃
が特に好ましい。Therefore, the reaction temperature is usually -10 to 50 ℃, even within -5 to 20 ℃
Is particularly preferable.
反応に当って使用する不活性有機溶媒としては、例えば
ｎ−ヘキサン、ｎ−ヘプタンなどの脂肪族炭化水素類、
例えばテトラヒドロフラン、ジエチルエーテルなどのエ
ーテル類、例えば酢酸エチルなどのエステル類が用いら
れる。Examples of the inert organic solvent used in the reaction include aliphatic hydrocarbons such as n-hexane and n-heptane,
For example, ethers such as tetrahydrofuran and diethyl ether, and esters such as ethyl acetate are used.
本発明の方法の具体的な一実施態様は、アンモニアを密
封型反応容器に仕込み、所定の反応温度に設定した後、
２−フェニルイソプロピルブロマイドを圧入する。圧入
後、必要に応じて熟成する。この様にして得られた２−
フェニルイソプロピルアミンは、脱アンモニア後公知の
方法により精製される。A specific embodiment of the method of the present invention is that ammonia is charged into a hermetically sealed reaction vessel, and a predetermined reaction temperature is set,
Press in 2-phenylisopropyl bromide. After press fitting, it is aged if necessary. 2 obtained in this way
Phenylisopropylamine is purified by a known method after deammonification.
＜発明の効果＞ 本発明の方法によれば、２−フェニルイソプロピルブロ
マイドより、２−フェニルイソプロピルアミンを高収率
で製造することができる。又、副生するα−メチルスチ
レンを未精製のまま、２−フェニルイソプロピルブロマ
イドの原料として用いることができる。<Effect of the Invention> According to the method of the present invention, 2-phenylisopropylamine can be produced in high yield from 2-phenylisopropyl bromide. In addition, α-methylstyrene produced as a by-product can be used as a raw material for 2-phenylisopropyl bromide as it is without being purified.
＜実施例＞ 次に、本発明を実施例により更に詳細に説明するが、本
発明はこれらの実施例に限定されるものではない。<Examples> Next, the present invention will be described in more detail with reference to Examples, but the present invention is not limited to these Examples.
尚、実施例中の部は、特に断わらない限り、重量部を表
わすものとする。In the examples, "parts" means "parts by weight" unless otherwise specified.
＜実施例−１＞ 内容積500容量部のステンレス製オートクレーブにアン
モニア101部を仕込み、０℃に冷却した後、２−フェニ
ルイソプロピルブロマイド246.3部を攪拌下、５時間で
圧入した。０℃、３時間熟成した後、脱アンモニアし、
水を加えた。水層のpHを13以上にした後、分液し、有機
層をガスクロ分析した。２−フェニルイソプロピルブロ
マイドの反応率100％、２−フェニルイソプロピルアミ
ン選択率90.5％、α−メチルスチレン選択率7.5％であ
った。<Example-1> 101 parts of ammonia was charged into a stainless steel autoclave having an internal volume of 500 parts by volume, cooled to 0 ° C, and then 246.3 parts of 2-phenylisopropyl bromide was injected under stirring for 5 hours. After aging at 0 ° C for 3 hours, deammonia is removed,
Water was added. After adjusting the pH of the aqueous layer to 13 or more, the layers were separated, and the organic layer was analyzed by gas chromatography. The reaction rate of 2-phenylisopropyl bromide was 100%, the selectivity of 2-phenylisopropylamine was 90.5%, and the selectivity of α-methylstyrene was 7.5%.
＜実施例−２＞ 内容積500容量部のステンレス製オートクレーブにアン
モニア101部を仕込み、７℃に冷却した後、２−フェニ
ルイソプロピルブロマイド246.3部を攪拌下、５時間で
圧入した。７℃、３時間熟成した後、脱アンモニアし、
水を加えた。水層のpHを13以上にした後、分液し、有機
層をガスクロ分析した。２−フェニルイソプロピルブロ
マイドの反応率100％、２−フェニルイソプロピルアミ
ンの選択率89.3％、α−メチルスチレン選択率8.0％で
あった。<Example-2> 101 parts of ammonia was charged into a stainless steel autoclave having an internal volume of 500 parts by volume, cooled to 7 ° C, and then 246.3 parts of 2-phenylisopropyl bromide was injected under stirring for 5 hours. After aging at 7 ° C for 3 hours, deammonia is removed,
Water was added. After adjusting the pH of the aqueous layer to 13 or more, the layers were separated, and the organic layer was analyzed by gas chromatography. The reaction rate of 2-phenylisopropyl bromide was 100%, the selectivity of 2-phenylisopropylamine was 89.3%, and the selectivity of α-methylstyrene was 8.0%.
＜実施例−３＞ 内容積500容量部のステンレス製オートクレーブにアン
モニア73.6部を仕込み、０℃に冷却した後、２−フェニ
ルイソプロピルブロマイド246.3部を攪拌下、５時間で
圧入した。０℃、３時間熟成した後、脱アンモニアし、
水を加えた。水層のpHを13以上にした後、分液し、有機
層をガスクロ分析した。２−フェニルイソプロピルブロ
マイドの反応率100％、２−フェニルイソプロピルアミ
ン選択率88.0％、α−メチルスチレン選択率9.4％であ
った。<Example-3> 73.6 parts of ammonia was charged into a stainless steel autoclave having an internal volume of 500 parts by volume, cooled to 0 ° C, and then 246.3 parts of 2-phenylisopropyl bromide was injected under stirring for 5 hours. After aging at 0 ° C for 3 hours, deammonia is removed,
Water was added. After adjusting the pH of the aqueous layer to 13 or more, the layers were separated, and the organic layer was analyzed by gas chromatography. The reaction rate of 2-phenylisopropyl bromide was 100%, the selectivity of 2-phenylisopropylamine was 88.0%, and the selectivity of α-methylstyrene was 9.4%.
＜実施例−４＞ 内容積500容量部のステンレス製オートクレーブにアン
モニア70.8部を仕込み、10℃にした後、２−フェニルイ
ソプロピルブロマイド118.4部を攪拌下、５時間で圧入
した。10℃、３時間熟成した後、脱アンモニアし、水を
加えた。水層のpHを13以上にした後、分液し、有機層を
ガスクロ分析した。２−フェニルイソプロピルブロマイ
ドの反応率100％、２−フェニルイソプロピルアミン選
択率93.2％、α−メチルスチレン選択率5.3％であっ
た。<Example-4> 70.8 parts of ammonia was charged into a stainless steel autoclave having an internal volume of 500 parts by volume, the temperature was adjusted to 10 ° C, and 118.4 parts of 2-phenylisopropyl bromide was press-fitted under stirring for 5 hours. After aging at 10 ° C for 3 hours, deammonification was performed and water was added. After adjusting the pH of the aqueous layer to 13 or more, the layers were separated, and the organic layer was analyzed by gas chromatography. The reaction rate of 2-phenylisopropyl bromide was 100%, the selectivity of 2-phenylisopropylamine was 93.2%, and the selectivity of α-methylstyrene was 5.3%.
＜実施例−５＞ 内容積500容量部のステンレス製オートクレーブにアン
モニア37.7部とｎ−ヘプタン100部を仕込み、０℃にし
た後、２−フェニルイソプロピルブロマイド126.1部を
攪拌下、５時間で圧入した。０℃、３時間熟成した後、
脱アンモニアし、水を加えた。水層のpHを13以上にした
後、分液し、有機層をガスクロ分析した。２−フェニル
イソプロピルブロマイドの反応率100％、２−フェニル
イソプロピルアミン選択率91.0％、α−メチルスチレン
選択率7.1％であった。<Example-5> 37.7 parts of ammonia and 100 parts of n-heptane were charged into a stainless steel autoclave having an inner volume of 500 parts by volume, the temperature was adjusted to 0 ° C, and 126.1 parts of 2-phenylisopropyl bromide was injected under stirring for 5 hours. . After aging at 0 ° C for 3 hours,
It was deammonified and water was added. After adjusting the pH of the aqueous layer to 13 or more, the layers were separated, and the organic layer was analyzed by gas chromatography. The reaction rate of 2-phenylisopropyl bromide was 100%, the selectivity of 2-phenylisopropylamine was 91.0%, and the selectivity of α-methylstyrene was 7.1%.
＜比較例−１＞ 内容積500容量部のステンレス製オートクレーブにアン
モニア101部を仕込み、50℃にした後、２−フェニルイ
ソプロピルクロライド191.1部を攪拌下、５時間で圧入
した。50℃、３時間熟成した後、脱アンモニアし、水を
加えた。水層のpHを13以上にした後、分液し、有機層を
ガスクロ分析した。２−フェニルイソプロピルクロライ
ドの反応率100％、２−フェニルイソプロピルアミンの
選択率59.0％、α−メチルスチレン選択率37.5％であっ
た。<Comparative Example-1> 101 parts of ammonia was charged into a stainless steel autoclave having an internal volume of 500 parts by volume, the temperature was raised to 50 ° C, and 191.1 parts of 2-phenylisopropyl chloride was press-fitted under stirring for 5 hours. After aging at 50 ° C. for 3 hours, deammonification was performed and water was added. After adjusting the pH of the aqueous layer to 13 or more, the layers were separated, and the organic layer was analyzed by gas chromatography. The reaction rate of 2-phenylisopropyl chloride was 100%, the selectivity of 2-phenylisopropylamine was 59.0%, and the selectivity of α-methylstyrene was 37.5%.
＜比較例−２＞ 内容積500容量部のステンレス製オートクレーブにアン
モニア101部を仕込み、０℃に冷却した後、２−フェニ
ルイソプロピルクロライド191.1部を攪拌下、５時間で
圧入した。０℃、３時間熟成した後、脱アンモニアし、
水を加えた。水層のpHを13以上にした後、分液し、有機
層をガスクロ分析した。２−フェニルイソプロピルクロ
ライドの反応率は２％であった。<Comparative Example-2> 101 parts of ammonia was charged into a stainless steel autoclave having an internal volume of 500 parts by volume, cooled to 0 ° C, and 191.1 parts of 2-phenylisopropyl chloride was injected under stirring for 5 hours. After aging at 0 ° C for 3 hours, deammonia is removed,
Water was added. After adjusting the pH of the aqueous layer to 13 or more, the layers were separated, and the organic layer was analyzed by gas chromatography. The reaction rate of 2-phenylisopropyl chloride was 2%.
Claims (4)
不活性有機溶媒の存在又は不存在下、アンモニアと反応
させることを特徴とする２−フェニルイソプロピルアミ
ンの製造方法。1. 2-Phenylisopropyl bromide,
A method for producing 2-phenylisopropylamine, which comprises reacting with ammonia in the presence or absence of an inert organic solvent.
ロマイド１モルに対し、２〜10モル反応させることを特
徴とする特許請求の範囲第１項に記載の２−フェニルイ
ソプロピルアミンの製造方法。2. The method for producing 2-phenylisopropylamine according to claim 1, wherein 2 to 10 mol of ammonia is reacted with 1 mol of 2-phenylisopropyl bromide.
ンモニアとを−10〜50℃の温度で反応させることを特徴
とする特許請求の範囲第１項及び第２項に記載の２−フ
ェニルイソプロピルアミンの製造方法。3. Production of 2-phenylisopropylamine according to claim 1 or 2, characterized in that 2-phenylisopropyl bromide and ammonia are reacted at a temperature of -10 to 50 ° C. Method.
ンモニアとを、−５〜20℃の温度で反応させることを特
徴とする特許請求の範囲第１項及び第２項に記載の２−
フェニルイソプロピルアミンの製造方法。4. 2-Phenylisopropyl bromide and ammonia are reacted at a temperature of -5 to 20 [deg.] C. according to claim 1 or 2.
Method for producing phenylisopropylamine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3518387A JPH0759536B2 (en) | 1987-02-17 | 1987-02-17 | Method for producing 2-phenylisopropylamine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3518387A JPH0759536B2 (en) | 1987-02-17 | 1987-02-17 | Method for producing 2-phenylisopropylamine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63201148A JPS63201148A (en) | 1988-08-19 |
| JPH0759536B2 true JPH0759536B2 (en) | 1995-06-28 |
Family
ID=12434731
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3518387A Expired - Fee Related JPH0759536B2 (en) | 1987-02-17 | 1987-02-17 | Method for producing 2-phenylisopropylamine |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0759536B2 (en) |
-
1987
- 1987-02-17 JP JP3518387A patent/JPH0759536B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63201148A (en) | 1988-08-19 |
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